19728-71-3

Basic information

• Product Name: methyl 3-methoxy-O,beta-dimethyl-L-tyrosinate
• Synonyms: methyl 3-methoxy-O,beta-dimethyl-L-tyrosinate;3-Methoxy-O,β-dimethyl-L-tyrosine methyl ester;Einecs 243-259-7
• CAS NO: 19728-71-3
• Molecular Formula: C₁₃H₁₉NO₄
• Molecular Weight: 253.29426
• EINECS: 243-259-7
• Mol File: 19728-71-3.mol

Chemical Properties

• Melting Point: 70-71 °C
• Boiling Point: 345.9°Cat760mmHg
• Flash Point: 128.1°C
• Appearance: /
• Density: 1.115g/cm³
• PKA: 6.69±0.25(Predicted)
• CAS DataBase Reference: methyl 3-methoxy-O,beta-dimethyl-L-tyrosinate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 3-methoxy-O,beta-dimethyl-L-tyrosinate(19728-71-3)
• EPA Substance Registry System: methyl 3-methoxy-O,beta-dimethyl-L-tyrosinate(19728-71-3)

Safety Data

• Hazardous Substances Data: 19728-71-3(Hazardous Substances Data)

Upstream product

• 81144-27-6 (2S,5R)-5-((E)-But-2-enyl)-2-(3,4-dimethoxy-benzyl)-3,6-dimethoxy-2-methyl-2,5-dihydro-pyrazine 
• 81136-58-5 (2S,5R)-2-(3,4-Dimethoxy-benzyl)-3,6-dimethoxy-2-methyl-5-prop-2-ynyl-2,5-dihydro-pyrazine 
• 81136-56-3 (2S,5R)-2-(3,4-Dimethoxy-benzyl)-3,6-dimethoxy-2-methyl-5-(3-methyl-but-2-enyl)-2,5-dihydro-pyrazine 
• 81136-57-4 (2S,5R)-2-(3,4-Dimethoxy-benzyl)-5-((2E,4E)-hexa-2,4-dienyl)-3,6-dimethoxy-2-methyl-2,5-dihydro-pyrazine 
• 81144-28-7 (2S,5R)-2-(3,4-Dimethoxy-benzyl)-3,6-dimethoxy-2-methyl-5-((E)-3-phenyl-allyl)-2,5-dihydro-pyrazine 
• 81177-53-9 (2S,5R)-5-Allyl-2-(3,4-dimethoxy-benzyl)-3,6-dimethoxy-2-methyl-2,5-dihydro-pyrazine 
• 81136-61-0 (2S,5R)-2-(3,4-Dimethoxy-benzyl)-5-(1-ethyl-1-methoxy-propyl)-3,6-dimethoxy-2-methyl-2,5-dihydro-pyrazine 
• 81136-63-2 (2S,5R)-2-(3,4-Dimethoxy-benzyl)-3,6-dimethoxy-5-(1-methoxy-cyclopentyl)-2-methyl-2,5-dihydro-pyrazine 
• 81136-60-9 (2S,5R)-2-(3,4-Dimethoxy-benzyl)-3,6-dimethoxy-5-(1-methoxy-1-methyl-propyl)-2-methyl-2,5-dihydro-pyrazine 
• 81136-64-3 (2S,5R)-2-(3,4-Dimethoxy-benzyl)-3,6-dimethoxy-5-(1-methoxy-cyclohexyl)-2-methyl-2,5-dihydro-pyrazine 
• 81136-62-1 (2S,5R)-2-(3,4-Dimethoxy-benzyl)-3,6-dimethoxy-5-(1-methoxy-1-propyl-butyl)-2-methyl-2,5-dihydro-pyrazine 
• 81136-71-2 [(S)-2-Amino-3-(3,4-dimethoxy-phenyl)-2-methyl-propionylamino]-acetic acid ethyl ester 
• 79448-86-5 (3S)-2,5-Dimethoxy-3-(3,4-dimethoxybenzyl)-3-methyl-3,6-dihydropyrazine 
• 132970-17-3 N-Boc-α-methyl-β-3,4-dimethoxyphenyl-L-alanine methylester 

Downstream Products

• 137394-68-4 C₂₀H₂₅NO₆S 
• 109522-07-8 (S)-2-amino-3-(3,4-dimethoxyphenyl)-2-methylpropionamide 
• 1428736-51-9 (2R,5S)-5-(3,4-dimethoxybenzyl)-5-methyl-2-(pyridine-2-yl)imidazolidine-4-one 
• 1428736-52-0 (2S,5S)-5-(3,4-dimethoxybenzyl)-5-methyl-2-(pyridine-2-yl)imidazolidine-4-one 
• 1428736-53-1 (2R,5S)-5-(3,4-dimethoxybenzyl)-2,5-dimethyl-2-(pyridine-2-yl)imidazolidine-4-one 
• 1428736-54-2 (2S,5S)-5-(3,4-dimethoxybenzyl)-2,5-dimethyl-2-(pyridine-2-yl)imidazolidine-4-one 
• 120346-38-5 α-methyl-β-3,4-dimethoxyphenyl-L-alanine methyl amide 

Relevant articles and documents

Mechanistic Insights into Enantioselective C-H Photooxygenation of Aldehydes via Enamine Catalysis

Organocatalytic photooxygenation of aldehydes at the α-position proceeds via enamine catalysis, though enamines should be easily oxidized by singlet oxygen respectively to amides and carbonyl compounds. Moreover, the formation of a zwitterionic enamine peroxide intermediate was postulated based on experimental and theoretical data. The reaction affords desired diols (after in situ reduction) in a decent yield and (S)- or (R)-enantioselectivity depending on a catalyst used. The (S)-enantiomer predominated in imidazolidinone-catalyzed reactions, while prolineamides assured the formation of the (R)-stereoisomer. DFT calculation suggests that the enamine-oxygen complex with the lowest energy has the E,s-cis conformation for the prolineamide derivative and E,s-trans for the imidazolidinone catalyst, explaining the opposite stereoselectivity in the photooxygenation reaction.

New applications of PhI(OAc)2 in synthesis: Total synthesis and SAR development of potent antitumor natural product psymberin/irciniastatin A

A novel PhI(OAc)2-mediated oxidative cyclization reaction is discovered for the synthesis of a-oxy N-acyl aminals and hemiaminals in good yields from readily synthesized N-acyl enamines. This methodology represents a cascade process to construct the core structure of the pederin family of natural products. The total synthesis of psymberin, a member of the pederin family, is accomplished using this ring-closure reaction as the key step. This new method is further showcased in the preparation of advanced psymberin analogues. The biological data of these analogues are presented. Georg Thieme Verlag Stuttgart.